Ethyl Acetate → 3-(4-Phenyl-1,3-oxazol-5-yl)propanoic acid

HRID 1982430Notes

Reaction equation

HRID 1982430 reaction equation
[Na].I[CH2:3][CH2:4][C:5]1[O:9][CH:8]=[N:7][C:6]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:16]([O:19]CC)(=[O:18])C>CS(C)=O>[C:10]1([C:6]2[N:7]=[CH:8][O:9][C:5]=2[CH2:4][CH2:3][C:16]([OH:19])=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 5360545SodiumHCID 233165895-(2-Iodoethyl)-4-phenyl-1,3-oxazole

Product 1

HCID 132932803-(4-Phenyl-1,3-oxazol-5-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Sodium cyannide (1.18 g) was dissolved in dimethyl sulfoxide (40 ml) and, under stirring, a solution of 5-(2-iodoethyl)-4-phenyloxazole (6.0 g) in dimethyl sulfoxide (20 ml) was added dropwise. The mixture was stirred for 2 hours, followed by addition of ice-water and extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off and the residual crude 4-phenyloxazole-5-propionitrile was dissolved in a mixture of ethanol (40 ml) and 2N sodium hydroxide (40 ml) and the solution was refluxed under stirring for 2 hours. The reaction mixture was concentrated, diluted with water and washed with dichloromethane. The aqueous layer was adjusted to pH 2 with hydrochloric acid and the resulting crystalline precipitate was collected by filtration and recrystallized from ethyl acetate and then from ethanol to give 4-phenyloxazole-5-propionic acid as prisms, yield 0.95 g (21.8%), m.p. 142°-143° C.

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was then distilled off
  5. dissolutionthe residual crude 4-phenyloxazole-5-propionitrile was dissolved in a mixture of ethanol (40 ml) and 2N sodium hydroxide (40 ml)
  6. temperaturethe solution was refluxed
  7. stirringunder stirring for 2 hours
  8. concentrationThe reaction mixture was concentrated
  9. additiondiluted with water
  10. washwashed with dichloromethane
  11. filtrationthe resulting crystalline precipitate was collected by filtration
  12. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ae20f14f6d3a46f9acba520b042a9bb8
Source dataset
uspto-grants-1986_06
Patent number
US04596816

Reaction notes

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